6 Things Not to Worry About On a First Date

You know those Internet-dating ads on TV, with their casual arm touches and delicious-looking pastas, the couple laughing at each other's jokes like they're on ecstasy? Fantasy. Most first dates are two-hour displays of nerves, insecurities and awkwardness—with occasional bathroom breaks. But I've learned, through much trial and error, that they don't have to be; they can actually be downright fun…and sexy. If you get nervous about a first date (or a second or third, for that matter), consider: He invited you/accepted your invitation to dinner, so he's not looking for a reason to rule you out. He wants to get to know who you are, show you who he is and find out who you both could be to each other. So skip the deep breaths, and never mind the warm-up glass of wine. If you want to relax and enjoy your date, just read Jake's handy list of things you don't have to worry about.

Don't worry about…wearing the right jeans.

Fashion eludes most dudes. So: Paige, J Brand, 7 For All Mankind—the guy is barely aware that these are even things, much less what they signify. When we look down, we're admiring your butt, not the label above the pocket.

Don't worry about…whether the date "means something."

Sometimes a cigar is just a cigar—and a date is just a date. Enjoy the food. Engage in banter. Flirt. Have fun. Because every minute you spend wondering whether this is the beginning of something or whether he's going to call you afterward is time you're not appreciating the citrusy prosecco, the pretty candlelit room and the fact that he's trying to make you laugh. (Laugh!)

Don't worry about…the Spanx and push-up bra you have on.

A reader recently wrote Jake asking whether guys feel duped if, once things have progressed to the clothing-removal stage, they discover the woman's been wearing a padded bra all along. Now, to be clear: You don't need such things. You're sexy without them, I promise. But you've got your reasons, so the answer is no, we don't consider a little foam padding to be a devious form of subterfuge, or Spanx to be code for "She's got self-esteem issues." Simply because we're not in it for the undergarments. As my friend Jeff says, "If we get you home, we don't care about what you're wearing under your clothes; we just want to get them off quickly and appear as smooth as possible doing it."

Don't worry about…whether he wants a family.

Yes, it's important that you and he have similar life goals—but not before you know that The Big Lebowski is his all-time favorite movie. My friend Lindsey recently said no to a second date with a really good guy because he "wasn't even thinking about marriage yet," while she wanted "to be married two years ago, like my friends." It's great that she knows what she wants, but trying to suss out a man's life goals on a first date will be transparent and self-defeating. How would you feel if one of the first things he asked was whether you wanted kids, and if not, why not? Maybe you dream of having five, or an organic farm in Vermont, or a life of world travel, but leave those conversations at least until after you've seen his lousy impression of The Dude.

Don't worry about…paying for dinner at the place he picked.

If it's a first date, and he asked, he's paying. Why? Because he wants this chance to impress you. There are exceptions, and I'm not one to trade in stereotypes, but in general, I think that when the check comes, the guy should grab it. And when he does, do the reach-for-the-wallet thing; it's a nice gesture. As is your offer to "get the next one" when he politely refuses—and, eventually, to pick one up, please.

Don't worry about…whether he's trying to get into your pants.

He probably is! But that doesn't mean you should feel pressured to jump into bed with him to keep his interest or to test whether you two have physical chemistry (a kiss can tell you that). Nor should you feel compelled to "make him work for it" or any of those clichés involving cows and milk and economics. And if he doesn't try anything, it doesn't mean he's not into you. He might be shy (been there), afraid of blowing it by rushing (been there) or scarred from his last girlfriend (definitely been there). Whether you decide to have sex on the first date or the eighth, or to wait until your wedding night, it's all good. And it's also fine if you don't have it all figured out before the check arrives. That's what the next date is for.